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Updated Oct 26, 2023

5 Tips for Training Leaders to Work With Remote Teams

Managing employees in various locations is different from leading an in-office team. Here's how to properly train remote leaders.

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Written By: Adam UzialkoBusiness Strategy Insider and Senior Editor
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This guide was reviewed by a Business News Daily editor to ensure it provides comprehensive and accurate information to aid your buying decision.

Table of Contents

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  • Managing and leading a remote team comes with special challenges and requires unique skills.
  • Proactive communication is essential for success when managers are working with a distributed workforce.
  • Remote-leadership courses can give you the skills you need to successfully manage remote workers.
  • This article is for business owners and leaders who want to learn how to improve their leadership skills in a remote work environment.

Remote work is on the rise, which means leaders must adapt to leading and developing teams from a distance. This new work environment requires a different set of skills than traditional in-office management. Leaders need to be prepared to address challenges — such as communication, teamwork and company culture — among a dispersed workforce. When leaders are prepared, the flexibility of remote work can benefit the entire organization. 

Tips for training leaders with remote teams

Training leaders to manage remote workers effectively is vital to the success of any remote work program, according to Sara Sutton, CEO and founder of FlexJobs. In general, a remote leader’s focus should be on results and processes rather than on face time, which is so often relied upon in traditional office settings.

Sutton and other leaders of remote workforces offered their best advice for managers to work effectively with dispersed teams.

Teach leaders proactive communication.

One of the most useful areas of remote leadership training is proactive communication among teams and colleagues, Sutton said.

“Proactive communication — taking the initiative to reach out when an idea, question or challenge comes up, rather than waiting to be asked or waiting for a scheduled meeting — can really help to develop a more transparent, open management process, as well as build trust and prevent problems from going unnoticed,” she said.

“It’s exponentially harder for a remote leader to manage a team, compared with a leader who is managing a team in person,” added Phil Shawe, co-founder and co-CEO of translation services company TransPerfect. “To manage a team from a remote location, it’s best to make a strong effort to keep in touch with that employee.”

Leaders can proactively communicate by holding regular and individual meetings to address questions and help solve problems (not just to give a laundry list of updates), and by setting guidelines so all team members know which communication method (e.g., email, phone, online chat or video conference) to use in certain circumstances. For instance, Shawe advised against using email to convey “feelings” or any important updates that might invite a lot of follow-up questions.

Bryan Miles, co-founder of BELAY, added that remote leaders must also learn to communicate the “why” — more than the “what,” “when” and “how” — of important tasks and projects. 

“When the leader is not accessible, any hardworking adults can fill in the blank of the ‘what,’ ‘when’ and ‘how’ when they know the ‘why,'” Miles said.

Prepare leaders to set clear expectations.

In an office environment, employees often learn more about expectations through a traditional orientation process. They also pick up on the actions of others, such as when people take lunch or what time they leave for the day. In a remote work environment, these important details are not always clear.

To develop a successful team, leaders need to clearly communicate expectations to new employees from day one. Leaders can set their employees up for success by sharing their expectations around workday start and end times, lunch schedules, video calls and response times.

In addition, it’s important that new employees know what is expected of them in their specific role. What should they accomplish in their first month on the job? What are the key priorities in their role? Leaders should also ask about employees’ expectations. By learning more about what an employee wants out of their new role, leaders can show they are taking an active interest in their employees’ careers and success at the company. 

Create a checklist that includes clear expectations and an overview of the typical workday, and have your leaders follow this list when onboarding a new employee to their department or team.

Help leaders translate the company culture.

Another big piece of the puzzle is training leaders to translate the company culture for their remote team members. Shawe noted that creating a culture that fosters true leadership is hard enough to do when you’re in the same office, and becomes even more difficult the more remote employees you have.

When Sutton started FlexJobs as a remote company, she was diligent about considering how to translate the best traditional office elements and activities to a virtual environment. She advised reaching out to employees regularly to engage in casual conversations like those that might happen spontaneously in a physical office.

Did You Know?Did you know
A study by FlexJobs found that a toxic company culture was the No. 1 reason people quit their jobs (at 62 percent of respondents).

Encourage an environment of recognition.

According to a Gallup study, employees who receive recognition from their leaders fewer than a few times a year are 74 percent more likely to say they do not plan to be at their organization in one year. 

In a remote environment, it’s easy for positive feedback and employee wins to slip through the cracks. Leaders can improve teamwork and set their teams up for success if they actively recognize accomplishments. Leaders can also set an example by encouraging team members to celebrate and thank one another during team meetings.

Encourage leaders to set up a recognition system for their team. This might mean a monthly individual award, or a team award to celebrate significant milestones and new ideas that prove successful. Options to show employees appreciation abound. You might recognize them on company social media pages or on internal team sites like Slack. 

A little recognition can go a long way in keeping employees happy and retaining top talent.

Bring people together.

Whether it’s once a month, once a quarter or twice a year, remote leaders should attend a meeting at the company headquarters, Shawe said. This way, they can interact with the rest of their team in person and receive sufficient training for the skills they need. In addition, remote leaders should use common conferences (industry or internal training) to increase face-to-face opportunities.

Sutton said leadership training needs to focus on “best practices,” regardless of whether the leader is remote or onsite.

“Successful leaders focus on communication and culture, challenge and empower their team members, focus on short- and long-term strategy, and the list can go on,” she said. “These are all the same approaches that I’ve used to lead in onsite roles.”

Companies should provide leaders with opportunities to bring their teams together, such as a meeting at the company headquarters or an industry-related professional development event.

Remote leadership training and courses

Remote leadership requires special skills, and there are courses and training that can teach you best practices for managing employees remotely and addressing the common issues that arise.

Remote Leadership Institute

Remote Leadership Institute provides courses, blog posts and other resources to help you learn to manage your team. There is a Remote Team Assessment tool to help you assess how well your team communicates and identify ways to maximize productivity.

The Remote Leadership Course Certificate Series includes six sessions and can be completed in as little as five weeks. Participants receive course visuals, materials and preassessment evaluations, as well as copies of The Long-Distance Leader: Rules for Remarkable Remote Leadership and Meet Like You Mean It: A Leader’s Guide to Painless and Productive Virtual Meetings


Workplaceless creates assignments that help you build the skills you’ll need as a remote leader. They include practical lessons with case studies and advice from experienced remote leaders. The company also offers guided facilitation sessions that can be customized to meet the needs of your team. Modules include Remote Team Culture, Conflict Management, and Learning and Development.

The course includes videos, interactive lessons, downloadable worksheets, assessments and a digital certification upon completion.


Evolve provides e-learning solutions for business owners. Courses are available for groups and individuals. You can also create custom bundles. Evolve recommends offering all remote employees the How to Work From Home Successfully course. 

Evolve’s remote leadership tool kit provides 18 microcourses in six modules. These include Introduction to the Remote Leader, Leading Effective Virtual Meetings, and Remote Coaching Feedback.

Remote How

Remote How’s online training program is a six-week course that you can complete at your own pace. It requires approximately two to three hours per week. The course includes six hours of videos, 20 assessments and cheat sheets, and three expert webinars.

The Managing Distributed Teams course includes a community forum, master classes, biweekly consulting sessions and a certificate upon completion.

Cornell University

Cornell University’s external education unit, eCornell, offers extensive training in leading remote teams through a new certificate program. The course takes three months to complete and requires a commitment of three to five hours per week. It is 100 percent online, and continuing education units are available upon completion. 

The Leading Remote Teams certificate includes the following coursework:

  • Building high-performing virtual teams
  • Launching virtual team projects
  • Virtual communication, constructive conflict, and collaboration
  • Decision-making and accountability
  • Diversity and cross-cultural teams
  • A three-day live leadership session 

A prepared leader is a successful leader

As remote and hybrid work models continue to become more popular, leaders must be prepared to succeed in this environment. Today, there are many resources to help leaders learn more about the challenges they may face while supporting and developing remote employees. If you learn about these challenges ahead of time and acquiring new skills, you will be better prepared to retain top talent and maintain a strong team regardless of everyone’s location.

Casey Conway contributed to this article. 

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Written By: Adam UzialkoBusiness Strategy Insider and Senior Editor
Adam Uzialko, senior editor of Business News Daily, is not just a professional writer and editor — he’s also an entrepreneur who knows firsthand what it’s like building a business from scratch. His experience as co-founder and managing editor of a digital marketing company imbues his work at Business News Daily with a perspective grounded in the realities of running a small business. Since 2015, Adam has reviewed hundreds of small business products and services, including contact center solutions, email marketing software and text message marketing software. Adam uses the products, interviews users and talks directly to the companies that make the products and services he covers. He specializes in digital marketing topics, with a focus on content marketing, editorial strategy and managing a team.
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